Triethylamine → 4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]-1-piperidine methanesulfonamide

HRID 612498Notes

Reaction equation

HRID 612498 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[OH:13].CC[N:22](CC)CC.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:27][S:28]([NH2:22])(=[O:30])=[O:29])[CH2:16][CH2:15]1)[OH:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 195953934-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]piperidine

Product 1

HCID 538127284-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]-1-piperidine methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-[2-(2,3-dimethoxyphenyl)-1-hydroxyethyl]piperidine (10.0 g, 0.037 mol) and Et3N (5.7 ml) in CH2Cl2 (75 ml) was cooled to 5° C. and methanesulfonyl chloride (3.6 g, 0.03 mol) was added dropwise so that the temperature did not rise above 10° C. The reaction was allowed to stand at ambient temperature for 1 h, and the reaction was concentrated in vacuo. The residue was treated with water, resulting in the formation of a white solid, which was collected to afford 10 g of the sulfonamide. The solid was recrystallized from toluene to yield the titled compound, and an additional recrystallization of this, gave 0.8 g of the analytically pure product as a white solid, mp 112-114° C.

Workup

  1. customdid not rise above 10° C
  2. concentrationthe reaction was concentrated in vacuo
  3. additionThe residue was treated with water
  4. customresulting in the formation of a white solid, which
  5. customwas collected

Sources & evidence

ORD record
ord-a3428258ae514e10b66c3d94994ecad6
Source dataset
uspto-grants-1999_12
Patent number
US06004982

Reaction notes

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